Episode #154: Remote Year President Sam Pessin on Diversity, Equity & Inclusion and Building the World’s Largest Work-Travel Program

Episode Summary

Sam Pessin talks about his international upbringing in London, Jerusalem and Beijing, and how that impacted his life and his passion for travel.  He then talks about his professional career trajectory and ultimately deciding to co-found Remote Year in 2015.  Sam takes us through the evolution of Remote Year, refining the customer experience, scaling it to over 100 employees by 2019, and being acquired by Selina in 2020.  He then describes the current Remote Year offerings, ranging from one week retreats and one month workations to 4 and 12 month work-travel programs with a community of location independent professionals.  Matt shares his experience on the 12-month Remote Year program in 2016 and why it was the best year of his life.   Sam then describes the customer experience on Remote Year programs today and discusses safety, inclusion, positive impact, local immersion, and community building.  Matt and Sam also discuss the Remote Year alumni “Citizenship” program and why it is one of the most valuable parts of the Remote Year experience.  Sam then talks about the company’s Diversity, Equity and Inclusion priorities, and the progress Remote Year has made on its DEI goals over the last two years.  He then opens up about the impact that the pandemic had on Remote Year, the acquisition by Selina in 2020, his current role as President, and his vision for the future of Remote Year.  Next, Sam talks about Remote Year’s process for hiring amazing people, building company culture in a remote environment, and gives his tips on executive leadership.  He then shares his personal productivity habits, how he manages stress, his biggest lessons learned from building Remote Year, and what he would do differently if he had to do it all over again.  And finally, Sam shares his #1 Remote Year memory.  FULL SHOW NOTES AVIALABLE AT: www.TheMaverickShow.com

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Sam Pessin

Sam Pessin is the co-founder and President of Remote Year, the world’s largest international work-travel program for location-independent professionals.  Originally from the U.S., Sam grew up in Beijing, Jerusalem and London before returning to the U.S. for college.  In 2015, Sam co-founded Remote Year, which went on to raise $12 million in their Series A round, scale to over 100 employees by 2019, and get acquired by Selina in 2020.  Today, Remote Year enables location-independent professionals to live and work in different cities around the world as part of an immersive cultural and community experience. Participants get to work and live like a local for 1, 4, or 12 months in some of the world’s most vibrant cities with a group of other professionals from different backgrounds and industries.  For a monthly fee, Remote Year plans all the logistics including flights, accommodations, workspace access with 24/7 wifi, as well as connecting you with locals and planning activities on the ground in each city.  Remote Year also offers “learn and travel” experiences as well as week-long retreats.  At the time of this recording, over 3,000 participants have gone through the Remote Year program.

What You'll Learn
  • What it’s like to participate on Remote Year’s international work-travel program
  • The current state of Diversity, Equity and Inclusion on Remote Year
  • Sam’s biggest business lessons from building and scaling Remote Year
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TOP 3 FAVORITE TRAVEL DESTINATIONS

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Time Stamped Show Notes

**Click the time stamp to jump directly to that point in the episode.

[3:47] Growing up as an Expat in Beijing, Jerusalem and London

[6:28] Sam’s Career Path and Moving to Mumbai, India

[8:00] Founding Remote Year in 2015

[12:00] The Evolution of Remote Year

[16:22] Remote Year’s 1-week Retreats

[17:27] Remote Year’s 1-month Workations

[18:13] Remote Year’s 4-month and-12 month work-travel programs

[18:37] Matt’s Experience on Remote Year’s 12-month program

[21:29] The Customer Experience on Remote Year Programs Today

[22:46] Safety, Inclusion and Community Building on Remote Year Programs

[25:59] Integrating Local Positive Impact into Remote Year Programs

[27:36] Local Immersion, Connection, and Remote Year’s City Teams

[29:10] Remote Year’s Alumni “Citizenship” Program

[34:58] Remote Year’s Commitment and Progress on Diversity, Equity and Inclusion

[41:37] The impact of the Pandemic on Remote Year and Being Acquired by Selina

[43:25] Sam’s Current Role as President of Remote Year

[45:14] Sam’s Vision for the Future of Remote Year

[46:24] Remote Year’s Hiring Process

[49:34] Building Company Culture in a Remote Environment

[52:48] Executive Leadership in Remote Companies

[54:10] Sam’s Productivity Habits and Routines

[55:41] How Sam Manages Stress as an Entrepreneur

[57:50] Sam’s Lessons from Building Remote Year and What He Would do Differently

[59:05] Sam’s #1 Remote Year Memory

[1:01:12] The Lightning Round

  • #1 Book Sam Recommends
  • #1 Person with Whom Sam Would Most Like To Have Dinner
  • Top 3 Favorite Travel Destinations
  • Top 3 Bucket List Destinations
  • #1 Piece of Advice Same Would Give to His 18 Year Old Self

[1:02:38] How to Learn More and Get a Discount on a Remote Year Program